We propose to incorporate the indole moiety into 4-oxo-3- quinolinecarboxylic acids, a new class of potent antibiotic agents. Indoles having amine groups substituted in all possible ring positions will be synthesized and utilized as precursors of the potential antibiotics. Condensation of these aminoindoles with beta-dicarbonyl adducts will provide acryaltes which may be cyclized to the final 4-quinolone structure. Antimicrobial susceptibility testing will take place under the auspices of subproject I. We will also complete the basic preparation of selected melatonin precursors and analogs and submit them to the National Cancer Institute for testing as cell mitosis inhibitors. Reduction of the previously prepared indoleacetonitriles and final acetylation of the products will yield the analogs. We will also continue to evaluate the scope of the reaction of indoles with sodium bisulfite due to its potential significance to indole and medicinal chemistry. To accomplish this work, we intend to involve students in all aspects of the synthesis and characterization of these chemical compounds which will utilize at least 15 different types of chemical reactions some of which may be first-time applications in a specific area. The project does provide room for expansion and/or more detailed examination of any particular facet of the research which may prove to warrant such.